Shogaol → Paradol

참여 물질

반응 단계

A solution of [6]-shogaol (276 mg, 1.0 mmol) in THF (2 mL) at rt was treated with 10% Pd/C (30 mg, 10% w/w) under H2. The mixture was stirred at rt overnight and filtered. The filtrate was concentrated under reduced pressure. The residue was loaded to preparative TLC (hexane/EtOAc=8:1) to give the title compound M11 as a yellow oil (272 mg, yield 98%); 1H NMR (600 MHz, CDCl3) δ 6.69 (1H, d, J=1.6 Hz, H-2′), 6.82 (1H, d, J=8.0 Hz, H-5′), 6.66 (1H, dd, J=8.0, 1.7 Hz, H-6′), 2.69 (2H, t, J=7.4 Hz, H-1), 2.82 (2H, t, J 7.4 Hz, H-2), 2.37 (1H, t, J=7.4 Hz, H-4), 1.54 (2H, m, H-5), 1.30-1.24 (8H, m, ranged from H-6 to H-9), 0.87 (3H, t, J=6.8 Hz, H-10), and 3.87 (3H, s, OMe-3′); positive APCIMS, m/z 279 [M+H]+.

출처 및 근거